Heterocyclic compound and organic light-emitting element using same

ABSTRACT

The present specification provides a heterocyclic compound and an organic light emitting device using the same.

TECHNICAL FIELD

This application claims priority to and the benefits of Korean PatentApplication No. 10-2013-0116594, filed with the Korean IntellectualProperty Office on Sep. 30, 2013, the entire contents of which areincorporated herein by reference.

The present disclosure relates to a heterocyclic compound and an organiclight emitting device using the same.

BACKGROUND ART

An organic light emission phenomenon is one of the examples convertingcurrent to visible light by an internal process of a specific organicmolecule. The principle of an organic light emission phenomenon is asfollows.

When an organic material layer is placed between an anode and a cathodeand voltage is applied between the two electrodes, electrons and holesflow into the organic material layer from the cathode and the anode,respectively. The electrons and the holes injected to the organicmaterial layer are recombined to form excitons, and light emits whenthese excitons fall back to the ground state. An organic light emittingdevice using such a principle is typically formed with a cathode, ananode, and an organic material layer placed therebetween, whichincludes, for example, a hole injection layer, a hole transfer layer, alight emitting layer and an electron transfer layer.

Materials used in organic light emitting devices are mostly pure organicmaterials or complex compounds in which organic materials and metalsform complexes, and may be divided into hole injection materials, holetransfer materials, light emitting materials, electron transfermaterials, electron injection materials and the like. Herein, as thehole injection material or the hole transfer material, organic materialshaving p-type properties, that is, readily oxidized and in anelectrochemically stable state when oxidized, are generally used.Meanwhile, as the electron injection material or the electron transfermaterial, organic materials having n-type properties, that is, readilyreduced and in an electrochemically stable state when reduced, aregenerally used. As the light emitting layer material, materials havingboth p-type properties and n-type properties, that is, in a stable statein both an oxidation and a reduction state, are preferable, andmaterials having high light emission efficiency that, when excitons areformed, convert the excitons to light are preferable.

Accordingly, the development of new organic materials has been requiredin the art.

PRIOR ART DOCUMENTS Patent Documents

Korean Patent Application Laid-Open Publication No. 2007-0092667

DISCLOSURE Technical Problem

An object of the present specification is to provide a heterocycliccompound and an organic light emitting device using the same.

Technical Solution

The present specification provides an organic light emitting deviceincluding a first electrode; a second electrode provided opposite to thefirst electrode; and one or more organic material layers including alight emitting layer provided between the first electrode and the secondelectrode, wherein one or more layers of the organic material layersinclude the heterocyclic compound represented by the following ChemicalFormula 1.

In Chemical Formula 1,

X is O or S,

R1 is deuterium; a halogen group; a nitrile group; a nitro group; ahydroxyl group; a carbonyl group; an ester group; an imide group; anamide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted alkylamine group; a substituted or unsubstitutedaralkylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted heteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroring group including one or more ofN, O and S atoms, and

R2 to R8 are the same as or different from each other, and eachindependently hydrogen; deuterium; a halogen group; a nitrile group; anitro group; a hydroxyl group; a carbonyl group; an ester group; animide group; an amide group; a substituted or unsubstituted alkyl group;a substituted or unsubstituted cycloalkyl group; a substituted orunsubstituted alkoxy group; a substituted or unsubstituted aryloxygroup; a substituted or unsubstituted alkylthioxy group; a substitutedor unsubstituted arylthioxy group; a substituted or unsubstitutedalkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted silyl group; a substituted or unsubstituted boron group; asubstituted or unsubstituted alkylamine group; a substituted orunsubstituted aralkylamine group; a substituted or unsubstitutedarylamine group; a substituted or unsubstituted heteroarylamine group; asubstituted or unsubstituted arylphosphine group; a substituted orunsubstituted phosphine oxide group; a substituted or unsubstituted arylgroup; or a substituted or unsubstituted heteroring group including oneor more of N, O and S atoms, or adjacent groups among R2 to R8 bond toeach other to form an aliphatic ring, an aromatic ring, an aliphaticheteroring or an aromatic heteroring, or form a spiro bond.

In addition, the present specification provides a heterocyclic compoundrepresented by the following Chemical Formula 3.

In Chemical Formula 3,

X is O or S,

R1 is deuterium; a halogen group; a nitrile group; a nitro group; ahydroxyl group; a carbonyl group; an ester group; an imide group; anamide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted alkylamine group; a substituted or unsubstitutedaralkylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted heteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroring group including one or more ofN, O and S atoms,

R2 to R8 are the same as or different from each other, and eachindependently hydrogen; deuterium; a halogen group; a nitrile group; anitro group; a hydroxyl group; a carbonyl group; an ester group; animide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted alkylamine group; a substituted or unsubstitutedaralkylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted heteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroring group including one or more ofN, O and S atoms, or adjacent groups among R2 to R8 bond to each otherto form an aliphatic ring, an aromatic ring, an aliphatic heteroring oran aromatic heteroring, or form a spiro bond, and

at least one of R2 to R8 is a substituted or unsubstituted alkyl group;a substituted or unsubstituted alkenyl group; a substituted orunsubstituted aryl group; a substituted or unsubstituted phosphine oxidegroup; or a substituted or unsubstituted heteroring group including oneor more of N, O and S atoms.

Advantageous Effects

A heterocyclic compound according to one embodiment of the presentspecification has a proper energy level, and an excellentelectrochemical stability and thermal stability. Accordingly, an organiclight emitting device including the compound provides high efficiencyand/or high driving stability.

DESCRIPTION OF DRAWINGS

FIGS. 1 to 5 are cross-sectional diagrams illustrating structures of anorganic light emitting device according to one embodiment of the presentinvention.

REFERENCE NUMERAL

-   -   1: Substrate    -   2: Anode    -   3: Hole Injection Layer    -   4: Hole Transfer Layer    -   5: Light Emitting Layer    -   6: Electron Transfer Layer    -   7: Cathode

MODE FOR DISCLOSURE

Hereinafter, the present specification will be described in more detail.

One embodiment of the present specification provides an organic lightemitting device including a heterocyclic compound represented byChemical Formula 1.

One embodiment of the present specification provides an organic lightemitting device including a first electrode; a second electrode providedopposite to the first electrode; and one or more organic material layersincluding a light emitting layer provided between the first electrodeand the second electrode, wherein one or more layers of the organicmaterial layers include the heterocyclic compound represented byChemical Formula 1.

Examples of the substituents are described below, however, thesubstituents are not limited thereto.

In the present invention, the term “substituted or unsubstituted” meansbeing substituted with one or more substituents selected from the groupconsisting of deuterium; a halogen group; a nitrile group; a nitrogroup; an imide group; an amide group; a hydroxyl group; a thiol group;an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; asilyl group; an arylalkenyl group; an aryl group; an aryloxy group; analkylthioxy group; an arylthioxy group; an alkylsulfoxy group; anarylsulfoxy group; a silyl group; a boron group; an alkylamine group; anaralkylamine group; an arylamine group; a heteroaryl group; a carbazolegroup; an aryl group; a fluorenyl group; an arylalkyl group; anarylalkenyl group; and a heteroring group including one or more of N, Oand S atoms, or having no substituents, or being substituted with asubstituent linking two or more substituents of the substituentsillustrated above, or having no substituents. For example, “asubstituent linking two or more substituents” may include a biphenylgroup. In other words, a biphenyl group may be interpreted as an arylgroup, or as a substituent linking 2 phenyl groups.

The term “substitution” means a hydrogen atom bonding to a carbon atomof a compound is changed to another substituent, and the position ofsubstitution is not limited as long as it is a position at which ahydrogen atom is substituted, that is, a position at which a substituentmay substitute, and when two or more substituents substitute, the two ormore substituents may be the same as or different from each other.

In the present specification, examples of the halogen group includefluorine, chlorine, bromine or iodine.

In the present specification, in the ester group, the oxygen of theester group may be substituted with a linear, branched or cyclic alkylgroup having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbonatoms. Specifically, compounds having the following structural formulaemay be included, but the compound is not limited thereto.

In the present specification, the number of carbon atoms of the imidegroup is not particularly limited, but is preferably 1 to 25.Specifically, compounds having the following structures may be included,but the compound is not limited thereto.

In the present specification, in the amide group, the nitrogen of theamide group may be once or twice substituted with hydrogen, a linear,branched or cyclic alkyl group having 1 to 25 carbon atoms, or an arylgroup having 6 to 25 carbon atoms. Specifically, compounds having thefollowing structural formulae may be included, but the compound is notlimited thereto.

In the present specification, the alkyl group may be linear or branched,and the number of carbon atoms is not particularly limited, but ispreferably 1 to 50. Specific examples thereof include methyl, ethyl,propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl,sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl,neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl,4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl,1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl,tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl,2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl,2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are notlimited thereto.

In the present specification, the cycloalkyl group is not particularlylimited, but preferably has 3 to 60 carbon atoms. Specific examplesthereof include cyclopropyl, cyclobutyl, cyclopentyl,3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl,3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl,3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl,cyclooctyl and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branchedor cyclic. The number of carbon atoms of the alkoxy group is notparticularly limited, but is preferably 1 to 20. Specific examplesthereof may include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy,n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy,isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy,n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and thelike, but are not limited thereto.

In the present specification, the alkenyl group may be linear orbranched, and although not particularly limited, the number of carbonatoms is preferably 2 to 40. Specific examples thereof may includevinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl,allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl,2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl,a stilbenyl group, a styrenyl group and the like, but are not limitedthereto.

When the aryl group is a monocyclic aryl group, the number of carbonatoms is not particularly limited, but is preferably 6 to 25. Specificexamples of the monocyclic aryl group may include a phenyl group, abiphenyl group, a terphenyl group and the like, but are not limitedthereto.

When the aryl group is a multicyclic aryl group, the number of carbonatoms is not particularly limited, but is preferably 10 to 24. Specificexample of the multicyclic aryl group may include a naphthyl group, ananthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group,a crycenyl group, a fluorenyl group and the like, but are not limitedthereto.

In the present specification, the fluorenyl group may be substituted,and adjacent substituents may bond to each other to form a ring.

When the fluorenyl group is substituted,

and the like may be included. However, the structure is not limitedthereto.

In the present specification, the silyl group specifically includes atrimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilylgroup, a vinyldimethylsilyl group, a propyldimethylsilyl group, atriphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and thelike, but is not limited thereto.

In the present specification, the number of carbon atoms of the aminegroup is not particularly limited, but is preferably 1 to 30. Specificexamples of the amine group include a methylamine group, a dimethylaminegroup, an ethylamine group, a diethylamine group, a phenylamine group, anaphthylamine group, a biphenylamine group, an anthracenylamine group, a9-methyl-anthracenylamine group, a diphenylamine group, aphenylnaphthylamine group, a ditolylamine group, a phenyltolylaminegroup, a triphenylamine group and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include asubstituted or unsubstituted monoarylamine group, a substituted orunsubstituted diarylamine group, or a substituted or unsubstitutedtriarylamine group. The aryl group in the arylamine group may be amonocyclic aryl group or a multicyclic aryl group. The arylamine groupincluding two or more aryl groups may include monocyclic aryl groups,multicyclic aryl groups, or monocyclic aryl groups and multicyclic arylgroups at the same time.

Specific examples of the arylamine group include phenylamine,naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine,4-methyl-naphthylamine, 2-methyl-biphenylamine,9-methyl-anthracenylamine, a diphenylamine group, a phenylnaphthylaminegroup, a ditolylamine group, a phenyltolylamine group, carbazole, atriphenylamine group and the like, but are not limited thereto.

In the present specification, examples of the arylphosphine groupinclude a substituted or unsubstituted monoarylphosphine group, asubstituted or unsubstituted diarylphosphine group, or a substituted orunsubstituted triarylphosphine group. The aryl group in thearylphosphine group may be a monocyclic aryl group or a multicyclic arylgroup. The arylphosphine group including two or more aryl groups mayinclude monocyclic aryl groups, multicyclic aryl groups, or monocyclicaryl groups and multicyclic aryl groups at the same time.

In the present specification, the heteroring group is a heteroring groupincluding one or more of O, N and S as a heteroatom, and although notparticularly limited, the number of carbon atoms is preferably 2 to 60.Examples of the heteroring group include a thiophene group, a furangroup, a pyrrole group, an imidazole group, a triazole group, an oxazolegroup, an oxadiazole group, a triazole group, a pyridyl group, abipyridyl group, a pyrimidyl group, a triazine group, a triazole group,an acridyl group, a pyridazine group, a pyrazinyl group, a qinolinylgroup, a quinazoline group, a quinoxalinyl group, a phthalazinyl group,a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinylgroup, an isoquinoline group, an indole group, a carbazole group, abenzoxazole group, a benzimidazole group, a benzothiazole group, abenzocarbazole group, a benzothiophene group, a dibenzothiophene group,a benzofuranyl group, a phenanthroline group, a thiazolyl group, anisoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, abenzothiazolyl group, a phenothiazinyl group, a dibenzofuranyl group andthe like, but are not limited thereto.

In the present specification, the aryl group in the aryloxy group, thearylthioxy group, the arylsulfoxy group and the aralkylamine group isthe same as the examples of the aryl group described above. Specificexamples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy,3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy,3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy,4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy,2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy,9-phenanthryloxy and the like, examples of the arylthioxy group includea phenylthioxy group, a 2-methylphenylthioxy group, a4-tert-butylphenylthioxy group and the like, and examples of thearylsulfoxy group include a benzenesulfoxy group, a p-toluenesulfoxygroup and the like, but the examples are not limited thereto.

In the present specification, the heteroaryl group in theheteroarylamine group may be the same as the examples of the heteroringgroup described above.

In the present specification, the alkyl group in the alkylthioxy groupand the alkylsulfoxy group is the same as the examples of the alkylgroup described above. Specific examples of the alkylthioxy groupinclude a methylthioxy group, an ethylthioxy group, a tert-butylthioxygroup, a hexylthioxy group, an octylthioxy group and the like, andexamples of the alkylsulfoxy group include a mesyl group, anethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group and thelike, but the examples are not limited thereto.

In the present specification, an “adjacent” group means a substituentsubstituting an atom directly linking to an atom substituted by thecorresponding substituent, a substituent most closely positionedsterically to the corresponding substituent, or another substituentsubstituting an atom substituted by the corresponding substituent. Forexample, two substituents substituting ortho positions in a benzenering, and two substituents substituting the same carbon in an aliphaticring may be interpreted as “adjacent” groups.

In one embodiment of the present specification, R1 is a substituted orunsubstituted alkyl group; a substituted or unsubstituted alkenyl group;a substituted or unsubstituted aryl group; a substituted orunsubstituted phosphine oxide group; or a substituted or unsubstitutedheteroring group including one or more of N, O and S atoms.

In one embodiment of the present specification, R1 is a substituted orunsubstituted methyl group; a substituted or unsubstituted ethyl group;a substituted or unsubstituted t-butyl group; a substituted orunsubstituted phenyl group; a substituted or unsubstituted naphthylgroup; a substituted or unsubstituted phenanthryl group; a substitutedor unsubstituted anthracene group; a substituted or unsubstitutedpyrenyl group; a substituted or unsubstituted perylenyl group; asubstituted or unsubstituted pyridine group; a substituted orunsubstituted benzoquinoline group; a substituted or unsubstitutedfluorenyl group; a substituted or unsubstituted triazine group; asubstituted or unsubstituted quinoxaline group; a substituted orunsubstituted carbazole group; a substituted or unsubstitutedbenzocarbazole group; a substituted or unsubstitutedbenzimidazoquinazoline group; a substituted or unsubstitutedphenanthroline group; a substituted or unsubstituted styrene group; or asubstituted or unsubstituted phosphine oxide group.

In one embodiment of the present specification, R2 to R8 are the same asor different from each other, and each dependently hydrogen; asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedalkenyl group; a substituted or unsubstituted aryl group; a substitutedor unsubstituted phosphine oxide group; or a substituted orunsubstituted heteroring group including one or more of N, O and Satoms.

In one embodiment of the present specification, R2 to R8 are the same asor different from each other, and each dependently hydrogen; an alkylgroup; an alkenyl group; an aryl group; a phosphine oxide group; or aheteroring group including one or more of N, O and S atoms, and

the alkyl group; the alkenyl group; the aryl group; the phosphine oxidegroup; and the heteroring group including one or more of N, O and Satoms are unsubstituted or substituted with one, two or moresubstituents selected from the group consisting of deuterium, a nitrilegroup, a substituted or unsubstituted alkyl group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted silane group, a substituted orunsubstituted phosphine oxide group, and a substituted or unsubstitutedheteroring group including one or more of N, O and S atoms, or two ormore substituents bond to each other to form an aliphatic ring, anaromatic ring, an aliphatic heteroring or an aromatic heteroring, orform a spiro bond.

In one embodiment of the present specification, R2 to R8 are the same asor different from each other, and each dependently hydrogen; asubstituted or unsubstituted phenyl group; a substituted orunsubstituted naphthyl group; a substituted or unsubstituted phenanthrylgroup; a substituted or unsubstituted anthracene group; a substituted orunsubstituted pyrenyl group; a substituted or unsubstituted perylenylgroup; a substituted or unsubstituted pyridine group; a substituted orunsubstituted benzoquinoline group; a substituted or unsubstitutedfluorenyl group; a substituted or unsubstituted triazine group; asubstituted or unsubstituted quinoxaline group; a substituted orunsubstituted carbazole group; a substituted or unsubstitutedbenzocarbazole group; a substituted or unsubstitutedbenzimidazoquinazoline group; a substituted or unsubstituted styrenegroup; or a substituted or unsubstituted phosphine oxide group.

In one embodiment of the present specification, at least one of R1 to R8is an alkyl group; an alkenyl group; an aryl group; a phosphine oxidegroup; or a heteroring group including one or more of N, O and S atoms,and

the alkyl group; the alkenyl group; the aryl group; the phosphine oxidegroup; and the heteroring group including one or more of N, O and Satoms are unsubstituted or substituted with one, two or moresubstituents selected from the group consisting of deuterium, a nitrilegroup, a substituted or unsubstituted alkyl group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted silane group, a substituted orunsubstituted phosphine oxide group, and a substituted or unsubstitutedheteroring group including one or more of N, O and S atoms, or two ormore substituents bond to each other to form an aliphatic ring, anaromatic ring, an aliphatic heteroring or an aromatic heteroring, orform a Spiro bond.

In one embodiment of the present specification, at least one of R1 to R8is a methyl group; an ethyl group; a t-butyl group; a phenyl group; anaphthyl group; a phenanthryl group; an anthracene group; a pyrenylgroup; a perylenyl group; a pyridine group; a benzoquinoline group; afluorenyl group; a spirobifluorenyl group; a triazine group; aquinoxaline group; a carbazole group; a benzocarbazole group; abenzimidazoquinazoline group; a styrene group; or a phosphine oxidegroup, and

the phenyl group; the naphthyl group; the phenanthryl group; theanthracene group; the pyrenyl group; the perylenyl group; the pyridinegroup; the benzoquinoline group; the fluorenyl group; the triazinegroup; the quinoxaline group; the carbazole group; the benzocarbazolegroup; the benzimidazoquinazoline group; the styrene group; and thephosphine oxide group are unsubstituted or substituted with one, two ormore substituents selected from the group consisting of deuterium, aphenyl group, a naphthyl group, a biphenyl group, a fluorenyl groupsubstituted with an alkyl group, a phenanthryl group, a pyridine group,a quinoline group, a phenyl group substituted with a nitrile group, adibenzofuran group, a dibenzothiophene group, a fluorenyl groupsubstituted with an alkyl group and a nitrile group, an anthracenylgroup substituted with a phenyl group, an anthracenyl group substitutedwith a naphthyl group, a phenanthryl group, a thiophene groupsubstituted with a phenyl group, a carbazole group, a benzimidazolegroup substituted with a phenyl group, a benzothiazole group, aphenanthroline group, and a silane group substituted with a phenylgroup, or substituents in the same carbon bond to each other to form aspiro bond.

In the present specification, the substituents in the same carbonbonding to each other to form a spiro bond means two or more rings beinglinked sharing one carbon atom, and the substituents in the same carbonmay bond to each other to form a fluorene structure or aspiroanthracenefluorene structure.

In one embodiment of the present specification, at least one of R1 to R8is any one of the following structures.

In another embodiment, R1 is any one of the structures shown above.

In one embodiment of the present specification, R2 is any one of thestructures shown above.

In another embodiment, R2 is hydrogen.

In one embodiment, R3 is any one of the structures shown above.

In another embodiment, R3 is hydrogen.

In one embodiment of the present specification, R4 is any one of thestructures shown above.

In another embodiment, R4 is hydrogen.

In another embodiment, R5 is any one of the structures shown above.

In another embodiment, R5 is hydrogen.

In one embodiment of the present specification, R6 is any one of thestructures shown above.

In another embodiment, R6 is hydrogen.

In another embodiment of the present specification, R7 is any one of thestructures shown above.

In another embodiment, R7 is hydrogen.

In one embodiment of the present specification, R8 is any one of thestructures shown above.

In another embodiment, R8 is hydrogen.

In one embodiment of the present specification, the heterocycliccompound represented by Chemical Formula 1 may be represented by any oneof the following Chemical Formulae 1-1-1 to 1-1-64 and 2-1-1 to 2-1-10.

The compounds in the present specification may be prepared based on thepreparation examples described below.

Specifically, according to one embodiment of the present specification,the heterocyclic compound of Chemical Formula 1 may be prepared througha cyclization reaction, and the heterocyclic compound represented byChemical Formula 1 or 3 may be prepared by reacting R1 to R8 substitutedwith boronic acid or a dioxaborolane group, however, the preparationmethod is not limited thereto.

In one embodiment of the present specification, the organic materiallayer includes an electron transfer layer, an electron injection layeror a layer carrying out electron transfer and electron injection at thesame time, and the electron transfer layer, the electron injection layeror the layer carrying out electron transfer and electron injection atthe same time includes the heterocyclic compound.

In one embodiment of the present specification, as an organic lightemitting device including a first electrode; a second electrode providedopposite to the first electrode; a light emitting layer provided betweenthe first electrode and the second electrode; and two or more organicmaterial layers provided between the light emitting layer and the firstelectrode, or between the light emitting layer and the second electrode,at least one of the two or more organic material layers includes theheterocyclic compound. In one embodiment, as the two or more organicmaterial layers, two or more may be selected from the group consistingof an electron transfer layer, an electron injection layer, a layercarrying out electron transfer and electron injection at the same timeand a hole blocking layer.

In one embodiment of the present specification, the organic materiallayer includes two or more electron transfer layers, and at least one ofthe two or more electron transfer layers includes the heterocycliccompound. Specifically, in one embodiment of the present specification,the heterocyclic compound may be included in one layer of the two ormore electron transfer layers, or in each of the two or more electrontransfer layers.

In addition, in one embodiment of the present specification, when theheterocyclic compound is included in each of the two or more electrontransfer layers, materials other than the heterocyclic compound may bethe same as or different from each other.

In one embodiment of the present specification, the electron transferlayer, the electron injection layer or the layer carrying out electrontransfer and electron injection at the same time is formed only with theheterocyclic compound.

In one embodiment of the present specification, the electron transferlayer, the electron injection layer or the layer carrying out electrontransfer and electron injection at the same time includes theheterocyclic compound as a p-type host, and an n-type dopant as adopant.

In one embodiment of the present specification, the n-type dopantincludes alkali metals, alkali metal compounds, alkaline earth metals,alkaline earth metal compounds, or combinations thereof.

In one embodiment of the present specification, as the n-type dopant,one, two or more are selected from the group consisting of Li, Na, K,Rb, Cs, Mg, Ca, Sr, Ba, La, Nd, Sm, Eu, Tb, Yb, LiF, Li₂O, CsF or thefollowing compounds.

In one embodiment of the present specification, the light emitting layerincludes the heterocyclic compound.

In one embodiment of the present specification, the light emitting layerincludes the heterocyclic compound as a host, and includes a phosphorousdopant compound as a dopant.

In one embodiment of the present specification, the phosphorous dopantcompound is represented by the following Chemical Formula 2.

In Chemical Formula 2,

M1 is Ir or Os,

L10, L11 and L12 are the same as or different from each other, and eachindependently any one of the following structures,

p, q, q′, r, s, t, u′, v′, w′, x′, a, b′, c′, d, d′, f, g, h′, j, j′ andk are each an integer of 0 to 4,

r′, s′, t′, u, v, w, x, y, y′ and e′ are each an integer of 0 to 6,

b, e, h, i, k′ and 1 are an integer of 0 to 3,

c and g′ are an integer of 0 to 2,

f′ is an integer of 0 to 5,

z is an integer of 0 to 8, and

R10 to R65 are the same as or different from each other, and eachindependently selected from the group consisting of hydrogen; deuterium;a halogen group; a cyano group; a substituted or unsubstituted C_(2˜10)alkylsilyl group; a substituted or unsubstituted C_(6˜30) arylsilylgroup; a substituted or unsubstituted C_(1˜10) alkyl group; asubstituted or unsubstituted C_(2˜10) alkenyl group; a substituted orunsubstituted C_(1˜10) alkoxy group; a substituted or unsubstitutedC_(6˜20) aryl group; and a substituted or unsubstituted C_(5˜20)heteroring group, or adjacent groups form a monocyclic or multicyclicaliphatic, aromatic, heteroaliphatic or heteroaromatic fused ring.

In one embodiment of the present specification, the phosphorous dopantcompound represented by Chemical Formula 2 is any one of the followingcompounds.

In one embodiment of the present specification, the organic materiallayer further includes one, two or more layers selected from the groupconsisting of a hole injection layer, a hole transfer layer, an electrontransfer layer, an electron injection layer, an electron blocking layerand a hole blocking layer.

The organic material layer of the organic light emitting device in thepresent specification may be formed as a monolayer structure, but mayalso be formed as a multilayer structure in which two or more organicmaterial layers are laminated. For example, the organic light emittingdevice of the present specification may have a structure including ahole injection layer, a hole transfer layer, a light emitting layer, anelectron transfer layer, an electron injection layer and the like as theorganic material layer. However, the structure of the organic lightemitting device is not limited thereto, and may include less numbers oforganic material layers.

In another embodiment, the organic light emitting device may be anorganic light emitting device having a structure in which an anode, oneor more organic material layers and a cathode are laminated inconsecutive order on a substrate (normal type).

In another embodiment, the organic light emitting device may be anorganic light emitting device having a structure in which a cathode, oneor more organic material layers and an anode are laminated inconsecutive order on a substrate (inverted type).

For example, the structures of an organic light emitting deviceaccording to the present invention are illustrated in FIGS. 1 to 5.

FIG. 1 illustrates the structure of an organic light emitting device inwhich an anode (2), a hole injection layer (3), a hole transfer layer(4), a light emitting layer (5), an electron transfer layer (6) and acathode (7) are laminated in consecutive order on a substrate (1). In astructure such as this, the compound represented by Chemical Formula 1may be included in the hole injection layer (3), the hole transfer layer(4), the light emitting layer (5) or the electron transfer layer (6).

FIG. 2 illustrates the structure of an organic light emitting device inwhich an anode (2), a hole injection layer (3), a hole transfer layer(4), a light emitting layer (5) and a cathode (7) are laminated inconsecutive order on a substrate (1). In a structure such as this, thecompound represented by Chemical Formula 1 may be included in the holeinjection layer (3), the hole transfer layer (4) or the light emittinglayer (5).

FIG. 3 illustrates the structure of an organic light emitting device inwhich an anode (2), a hole transfer layer (4), a light emitting layer(5), an electron transfer layer (6) and a cathode (7) are laminated inconsecutive order on a substrate (1). In a structure such as this, thecompound represented by Chemical Formula 1 may be included in the holetransfer layer (4), the light emitting layer (5) or the electrontransfer layer (6).

FIG. 4 illustrates the structure of an organic light emitting device inwhich an anode (2), a light emitting layer (5), an electron transferlayer (6) and a cathode (7) are laminated in consecutive order on asubstrate (1). In a structure such as this, the compound represented byChemical Formula 1 may be included in the light emitting layer (5) orthe electron transfer layer (6).

FIG. 5 illustrates the structure of an organic light emitting device inwhich an anode (2), a light emitting layer (5) and a cathode (7) arelaminated in consecutive order on a substrate (1). In a structure suchas this, the compound represented by Chemical Formula 1 may be includedin the light emitting layer (5).

The organic light emitting device of the present specification may beprepared using materials and methods known in the art, except that oneor more layers of the organic material layers include the compound ofthe present specification, that is, the heterocyclic compound.

For example, the organic light emitting device of the presentspecification may be prepared by laminating a first electrode, anorganic material layer and a second electrode in consecutive order on asubstrate. Herein, the organic light emitting device may be prepared byforming an anode on the substrate by depositing a metal, a metal oxidehaving conductivity, or alloys thereof using a physical vapor deposition(PVD) method such as a sputtering method or an e-beam evaporationmethod, forming the organic material layer including a hole injectionlayer, a hole transfer layer, a light emitting layer and an electrontransfer layer thereon, and then depositing a material capable of beingused as a cathode thereon. In addition to this method, the organic lightemitting device may be prepared by depositing a cathode material, anorganic material layer and an anode material in consecutive order on asubstrate.

In addition, the heterocyclic compound may be formed as the organicmaterial layer using a solution coating method as well as a vacuumdeposition method when the organic light emitting device is prepared.Herein, the solution coating method means spin coating, dip coating,doctor blading, ink jet printing, screen printing, a spray method, rollcoating and the like, but is not limited thereto.

In one embodiment of the present specification, the first electrode is acathode, and the second electrode is an anode.

In one embodiment of the present specification, the first electrode isan anode, and the second electrode is a cathode.

The substrate may be selected considering optical properties andphysical properties as necessary. For example, the substrate ispreferably transparent. The substrate may be formed with hard materials,but may also be formed with flexible materials such as plastic.

The substrate material may include, in addition to glass and a quartzplate, polyethyleneterephthalate (PET), polyethylene naphthalate (PEN),polypropylene (PP), polyimide (PI), polycarbonate (PC), polystyrene(PS), polyoxymethylene (POM), an acrylonitrile styrene copolymer (AS)resin, an acrylonitrile butadiene styrene copolymer (ABS) resin,triacetyl cellulose (TAC) and polyarylate (PAR) and the like, but is notlimited thereto.

As the cathode material, a material having small work function isnormally preferable so that electron injection to an organic materiallayer is smooth. Specific examples of the cathode material includemetals such as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloysthereof; multilayer structure materials such as LiF/Al or LiO₂/Al, andthe like, but are not limited thereto.

As the anode material, a material having large work function is normallypreferable so that hole injection to the organic material layer issmooth. Specific examples of the anode material capable of being used inthe present specification include metals such as vanadium, chromium,copper, zinc and gold, or alloys thereof; metal oxides such as zincoxides, indium oxides, indium tin oxides (ITO) and indium zinc oxide(IZO); combinations of metals and oxides such as ZnO:Al or SnO₂:Sb;conductive polymers such as poly(3-methylthiophene),poly[3,4-(ethylen-1,2-dioxy)thiophene] (PEDOT), polypyrrole andpolyaniline, and the like, but are not limited thereto.

The hole transfer layer is a layer that receives holes from a holeinjection layer and transfers the holes to a light emitting layer, andas the hole transfer material, a material capable of receiving the holesfrom an anode or a hole injection layer, moving the holes to a lightemitting layer, and having high mobility for the holes, is suitable.Specific examples thereof include an arylamin-based organic material, aconductive polymer, a block copolymer having conjugated parts andnon-conjugated parts together, and the like, but are not limitedthereto.

The hole injection layer is a layer that injects holes from anelectrode, and the hole injection material is preferably a compound thathas an ability to transfer holes, therefore, has a hole injection effectin an anode, has an excellent hole injection effect for a light emittinglayer or a light emitting material, prevents excitons generated in thelight emitting layer from moving to an electron injection layer or anelectron injection material, and in addition, has an excellent thin filmforming ability. The highest occupied molecular orbital (HOMO) of thehole injection material is preferably in between the work function of ananode material and the HOMO of surrounding organic material layers.Specific examples of the hole injection material include a metalporphyrin, oligothiophene, an arylamin-based organic material, aphthalocyanine derivative, a hexanitrile hexazatriphenylen-based organicmaterial, a quinacridon-based organic material, a perylen-based organicmaterial, anthraquinone, and a polyanilin- and a polythiophen-basedconductive polymer, and the like, but are not limited thereto.

The light emitting material is a material capable of emitting light in avisible light region by receiving holes and electrons from a holetransfer layer and an electron transfer layer, respectively, and bindingthe holes and the electrons, and is preferably a material havingfavorable quantum efficiency for fluorescence or phosphorescence.Specific examples thereof include a 8-hydroxy-quinoline aluminum complex(Alq₃); a carbazole-based compound; a dimerized styryl compound; BAlq; a10-hydroxybenzo quinolin-metal compound; a benzoxazole-, a benzthiazole-and a benzimidazole-based compound; a poly(p-phenylenevinylene)(PPV)-based polymer; a spiro compound; polyfluorene, rubrene, and thelike, but are not limited thereto.

The light emitting layer may include a host material and a dopantmaterial. The host material includes a fused aromatic ring derivative, aheteroring-containing compound or the like. Specifically, the fusedaromatic ring derivative includes an anthracene derivative, a pyrenederivative, a naphthalene derivative, a pentacene derivative, aphenanthrene compound, a fluoranthene compound and the like, and theheteroring-containing compound includes a carbazole derivative, adibenzofuran derivative, a ladder-type furan compound, a pyrimidinederivative and the like, but the material is not limited thereto.

The dopant material includes an aromatic amine derivative, a styrylaminecompound, a boron complex, a fluoranthene compound, a metal complex, andthe like. Specifically, the aromatic amine derivative is a fusedaromatic ring derivative having a substituted or unsubstituted arylaminogroup and includes arylamino group-including pyrene, anthracene,crycene, periflanthene and the like, and the styrylamine compound is acompound in which substituted or unsubstituted arylamine is substitutedwith at least one arylvinyl group, and one, two or more substituentsselected from the group consisting of an aryl group, a silyl group, analkyl group, a cycloalkyl group and an arylamino group are substitutedor unsubstituted. Specifically, styrylamine, styryldiamine,styryltriamine, styryltetramine or the like is included, but thestyrylamine compound is not limited thereto. In addition, the metalcomplex includes an iridium complex, a platinum complex or the like, butis not limited thereto.

The electron transfer layer is a layer that receives electrons from anelectron injection layer and transfers the electrons to a light emittinglayer, and as the electron transfer material, a material capable offavorably receiving electrons from a cathode, moving the electrons to alight emitting layer, and having high mobility for the electrons, issuitable. Specific examples thereof include an Al complex of8-hydroxyquinoline; a complex including Alq3; an organic radicalcompound; a hydroxyflavon-metal complex and the like, but are notlimited thereto. The electron transfer layer may be used together withany desired cathode material as used according to existing technologies.Particularly, examples of the suitable cathode material include commonmaterials that have small work function, and in which an aluminum layeror a silver layer follows. Specifically the cathode material includescesium, barium, calcium, ytterbium and samarium, and in each case, analuminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from anelectrode, and the electron injection material is preferably a compoundthat has an ability to transfer electrons, has an electron injectioneffect from a cathode and has an excellent electron injection effect fora light emitting layer or a light emitting material, prevents excitonsgenerated in the light emitting layer from moving to a hole injectionlayer, and in addition, has an excellent thin film forming ability.Specific examples thereof include fluorenone, anthraquinodimethane,diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole,imidazole, perylene tetracarboxylic acid, fluorenylidene methane,anthrone or the like, and derivatives thereof, a metal complex compound,a nitrogen-containing 5-membered ring derivative, and the like, but arenot limited thereto.

The metal complex compound may include 8-hydroxyquinolinato lithium,bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)berylium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but is not limited thereto.

The hole blocking layer is a layer that blocks holes from reaching acathode, and may generally be formed under the same condition as thehole injection layer. Specific examples thereof include an oxadiazolederivative or a triazole derivative, a phenanthroline derivative, BCP,an aluminum complex and the like, but are not limited thereto.

The organic light emitting device according to the present specificationmay be a top-emission type, a bottom-emission type or a dual-emissiontype depending on the materials used.

In one embodiment of the present specification, the heterocycliccompound may be included in an organic solar cell or an organictransistor in addition to an organic light emitting device.

One embodiment of the present specification provides a heterocycliccompound represented by the following Chemical Formula 3.

In Chemical Formula 3,

X is O or S,

R1 is deuterium; a halogen group; a nitrile group; a nitro group; ahydroxyl group; a carbonyl group; an ester group; an imide group; anamide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted alkylamine group; a substituted or unsubstitutedaralkylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted heteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroring group including one or more ofN, O and S atoms,

R2 to R8 are the same as or different from each other, and eachindependently hydrogen; deuterium; a halogen group; a nitrile group; anitro group; a hydroxyl group; a carbonyl group; an ester group; animide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted alkylamine group; a substituted or unsubstitutedaralkylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted heteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroring group including one or more ofN, O and S atoms, or adjacent groups among R2 to R8 bond to each otherto form an aliphatic ring, an aromatic ring, an aliphatic heteroring oran aromatic heteroring, or form a spiro bond, and

at least one of R2 to R8 is a substituted or unsubstituted alkyl group;a substituted or unsubstituted alkenyl group; a substituted orunsubstituted aryl group; a substituted or unsubstituted phosphine oxidegroup; or a substituted or unsubstituted heteroring group including oneor more of N, O and S atoms.

In the heterocyclic compound represented by Chemical Formula 3, thesubstituents may be the same as the substituents described above, exceptthat at least one of R2 to R8 is a substituted or unsubstituted alkylgroup; a substituted or unsubstituted alkenyl group; a substituted orunsubstituted aryl group; a substituted or unsubstituted phosphine oxidegroup; or a substituted or unsubstituted heteroring group including oneor more of N, O and S atoms.

In one embodiment of the present specification, at least one of R2 to R8is selected from among the following structures.

In one embodiment of the present specification, R2 is any one of thestructures shown above.

In another embodiment, R2 is hydrogen.

In one embodiment of the present specification, R3 is any one of thestructures shown above.

In another embodiment, R3 is hydrogen.

In one embodiment of the present specification, R4 is any one of thestructures shown above.

In another embodiment, R4 is hydrogen.

In one embodiment of the present specification, R5 is any one of thestructures shown above.

In another embodiment, R5 is hydrogen.

In one embodiment of the present specification, R6 is any one of thestructures shown above.

In another embodiment, R6 is hydrogen.

In one embodiment of the present specification, R7 is any one of thestructures shown above.

In another embodiment, R7 is hydrogen.

In one embodiment of the present specification, R8 is any one of thestructures shown above.

In another embodiment, R8 is hydrogen.

In one embodiment of the present specification, the heterocycliccompound represented by Chemical Formula 3 is represented by any one ofthe following structures.

In another embodiment of the present specification, the heterocycliccompound represented by Chemical Formula 1 is represented by any one ofthe following structures.

One embodiment of the present specification may provide an organic lightemitting device including at least one of the compounds shown above.

In one embodiment of the present specification, the heterocycliccompound represented by Chemical Formula 3 is represented by any one ofthe following structures.

In another embodiment of the present specification, the heterocycliccompound represented by Chemical Formula 1 is represented by any one ofthe following structures.

One embodiment of the present specification may provide an organic lightemitting device including at least one of the compounds shown above.

In the present specification the organic light emitting device includingthe heterocyclic compound represented by Chemical Formula 3 is the sameas the organic light emitting device defined above.

The preparation of the heterocyclic compound represented by ChemicalFormula 1 and the organic light emitting device including theheterocyclic compound will be described in detail in the followingexamples. However, the following examples are for illustrative purposesonly, and the scope of the present specification is not limited thereto.

SYNTHESIS EXAMPLE Synthesis Example 1 Synthesis of Chemical Formula1-2-1

Synthesis Example 1-1 Synthesis of Compound 1-A

After 2-chloro-1,3-dinitrobenzene (30 g, 148.1 mmol) was dissolved inanhydrous ethanol (200 ml), the mixture was stirred under nitrogen.2-Amino-5-bromophenol (36.2 g, 192.5 mmol) and anhydrous sodium acetate(21.0 g, 255.8 mmol) were added thereto. The above solution was refluxedfor 2 hours, and then cooled to room temperature when the reaction wascomplete. The precipitated solids were washed until the filtrate becamecolorless, and dried to obtain Compound 1-A (45.6 g, yield 87%; MS:[M+H]⁺=353).

Synthesis Example 1-2 Synthesis of Compound 1-B

Compound 1-A (45.6 g, 128.9 mmol) was placed in an aqueous 1% sodiumhydroxide (NaOH) solution (850 ml), and the mixture was refluxed for 30minutes. After the result was cooled to room temperature, the producedsolids were filtered under reduced pressure while being washed with hotwater until the solids became neutral, and then the solids were dried toobtain Compound 1-B (37.6 g, yield 95%; MS: [M+H]⁺=306).

Synthesis Example 1-3 Synthesis of Compound 1-C

After Compound 1-B (32.4 g, 105.4 mmol) was dissolved in ethanol (30ml), 10% Pd—C (1.12 g, 10.5 mmol) was added and dispersed thereto, andthe mixture was cooled to 0° C. Hydrazine monohydrate (25 ml) was slowlyadded dropwise thereto. The mixture was heated for 30 minutes at 50° C.After the reaction was complete, the reaction product was cooled to roomtemperature, filtered using ethanol, and the filtrate was vacuumdistilled to obtain Compound 1-C (27.7 g, yield 95.0%; ms: [M+H]⁺=276).

Synthesis Example 1-4 Synthesis of Compound 1-D

Compound 1-C (27.7 g, 100.0 mmol) and acetaldehyde (5.6 ml, 100.0 mmol)were refluxed for 1 hour in ethyl acetate (150 ml). After the ethylacetate was removed under reduced pressure, the result was dissolved inchloroform (250 ml), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)(25.0 g, 110.1 mmol) was added thereto. The mixture was stirred for 1hour at room temperature. The black solids obtained by vacuum distillingthe mixture was columned using a tetrahydrofuran/hexane (THF/Hexane:1/3)solution to obtain Compound 1-D (22.9 g, yield 76.0%; MS: [M+H]⁺=300).

Synthesis Example 1-5 Synthesis of Chemical Formula 1-2-1

Compound 1-D (15.1 g, 50.0 mmol) and (10-phenylanthracen-9-yl)boronicacid (14.9 g, 50.0 mmol) were dissolved in tetrahydrofuran (THF). A 2 Mpotassium carbonate (K₂CO₃) solution (72 mL) andtetrakis(triphenylphosphine) palladium(0) (1.10 g, 1.91 mmol) were addedthereto, and the result was refluxed for 12 hours. After the reactionwas complete, the result was cooled to room temperature, filtered, andthen washed several times with water and ethanol. The filtered solidproduct was recrystallized using chloroform and ethyl acetate to obtaina compound of Chemical Formula 1-2-1 (15.2 g, yield 64%; MS:[M+H]⁺=475).

Synthesis Example 2 Synthesis of Chemical Formula 1-3-1

Synthesis Example 2-1 Synthesis of Compound 2-A

Compound 2-A (25.2 g, yield 80.0%; MS: [M+H]⁺=315) was obtained in thesame manner as in Synthesis Example 1-4 except that propionaldehyde (7.2ml, 100.0 mmol) was used instead of acetaldehyde.

Synthesis Example 2-2 Synthesis of Chemical Formula 1-3-1

A compound of Chemical Formula 1-3-1 (17.3 g, yield 71%; MS: [M+H]⁺=489)was obtained in the same manner as in Synthesis Example 1-5 except thatCompound 2-A (15.8 g, 50.0 mmol) was used instead of Compound 1-D.

Synthesis Example 3 Synthesis of Chemical Formula 1-3-4

A compound of Chemical Formula 1-3-4 (22.9 g, yield 81%; MS: [M+H]⁺=565)was obtained in the same manner as in Synthesis Example 1-5 except thatCompound 2-A (15.8 g, 50.0 mmol) was used instead of Compound 1-D, and(10-([1,1′-biphenyl]-4-yl)anthracen-9-yl)boronic acid (18.7 g, 50.0mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 4 Synthesis of Chemical Formula 1-3-5

A compound of Chemical Formula 1-3-5 (21.8 g, yield 72%; MS: [M+H]⁺=605)was obtained in the same manner as in Synthesis Example 1-5 except thatCompound 2-A (15.8 g, 50.0 mmol) was used instead of Compound 1-D, and(10-(9,9-dimethyl-9H-fluoren-2-yl)anthracen-9-yl)boronic acid (20.7 g,50.0 mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 5 Synthesis of Chemical Formula 1-3-6

A compound of Chemical Formula 1-3-6 (18.6 g, yield 66%; MS: [M+H]⁺=565)was obtained in the same manner as in Synthesis Example 1-5 except thatCompound 2-A (15.8 g, 50.0 mmol) was used instead of Compound 1-D, and(10-([1,1′-biphenyl]-3-yl)anthracen-9-yl)boronic acid (18.7 g, 50.0mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 6 Synthesis of Chemical Formula 1-3-12

A compound of Chemical Formula 1-3-12 (17.7 g, yield 69%; MS:[M+H]⁺=514) was obtained in the same manner as in Synthesis Example 1-5except that Compound 2-A (15.8 g, 50.0 mmol) was used instead ofCompound 1-D, and (10-(4-cyanophenyl)anthracen-9-yl)boronic acid (16.2g, 50.0 mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 7 Synthesis of Chemical Formula 1-3-18

A compound of Chemical Formula 1-3-18 (21.2 g, yield 75%; MS:[M+H]⁺=565) was obtained in the same manner as in Synthesis Example 1-5except that Compound 2-A (15.8 g, 50.0 mmol) was used instead ofCompound 1-D, and (3-(10-phenylanthracen-9-yl)phenyl)boronic acid (18.7g, 50.0 mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 8 Synthesis of Chemical Formula 1-3-19

A compound of Chemical Formula 1-3-19 (20.9 g, yield 74%; MS:[M+H]⁺=565) was obtained in the same manner as in Synthesis Example 1-5except that Compound 2-A (15.8 g, 50.0 mmol) was used instead ofCompound 1-D, and2-(9,10-diphenylanthracen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(22.8 g, 50.0 mmol) was used instead of (10-phenylanthracen-9-yl)boronicacid.

Synthesis Example 9 Synthesis of Chemical Formula 1-3-26

A compound of Chemical Formula 1-3-26 (17.8 g, yield 81%; MS:[M+H]⁺=439) was obtained in the same manner as in Synthesis Example 1-5except that Compound 2-A (15.8 g, 50.0 mmol) was used instead ofCompound 1-D, and (4-(naphthalen-2-yl)phenyl)boronic acid (12.4 g, 50.0mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 10 Synthesis of Chemical Formula 1-3-28

A compound of Chemical Formula 1-3-28 (15.7 g, yield 72%; MS:[M+H]⁺=439) was obtained in the same manner as in Synthesis Example 1-5except that Compound 2-A (15.8 g, 50.0 mmol) was used instead ofCompound 1-D, and (3,8-dihydropyren-4-yl)boronic acid (12.4 g, 50.0mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 11 Synthesis of Chemical Formula 1-3-29

A compound of Chemical Formula 1-3-29 (16.8 g, yield 69%; MS:[M+H]⁺=487) was obtained in the same manner as in Synthesis Example 1-5except that Compound 2-A (15.8 g, 50.0 mmol) was used instead ofCompound 1-D, and perylen-3-ylboronic acid (14.8 g, 50.0 mmol) was usedinstead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 12 Synthesis of Chemical Formula 1-3-30

A compound of Chemical Formula 1-3-30 (12.4 g, yield 57%; MS:[M+H]⁺=437) was obtained in the same manner as in Synthesis Example 1-5except that Compound 2-A (15.8 g, 50.0 mmol) was used instead ofCompound 1-D, and fluoranthen-3-ylboronic acid (12.3 g, 50.0 mmol) wasused instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 13 Synthesis of Chemical Formula 1-3-34

A compound of Chemical Formula 1-3-34 (18.4 g, yield 67%; MS:[M+H]⁺=551) was obtained in the same manner as in Synthesis Example 1-5except that Compound 2-A (15.8 g, 50.0 mmol) was used instead ofCompound 1-D, and 9,9′-spirobi[fluoren]-2-ylboronic acid (18.0 g, 50.0mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 14 Synthesis of Chemical Formula 1-4-1

Synthesis Example 14-1 Synthesis of Compound 14-A

Compound 14-A (31.3 g, yield 86%; MS: [M+H]⁺=363) was obtained in thesame manner as in Synthesis Example 1-4 except that benzaldehyde (10.6g, 100.0 mmol) was used instead of acetaldehyde.

Synthesis Example 14-2 Synthesis of Chemical Formula 1-4-1

A compound of Chemical Formula 1-4-1 (19.4 g, yield 72%; MS: [M+H]⁺=537)was obtained in the same manner as in Synthesis Example 1-5 except thatCompound 14-A (18.2 g, 50.0 mmol) was used instead of Compound 1-D.

Synthesis Example 15 Synthesis of Chemical Formula 1-1-25

Synthesis Example 15-1 Synthesis of Compound 15-A

Compound 15-A (30.8 g, yield 91%; MS: [M+H]⁺=229) was obtained in thesame manner as in Synthesis Example 1-1 and Synthesis Example 1-2 exceptthat 2-aminobromophenol (21.0 g, 192.5 mmol) was used instead of2-amino-5-bromophenol.

Synthesis Example 15-2 Synthesis of Compound 15-B

Compound 15-B (20.3 g, yield 97%; MS: [M+H]⁺=199) was obtained in thesame manner as in Synthesis Example 1-3 except that Compound 15-A (24.1g, 105.4 mmol) was used instead of Compound 1-B.

Synthesis Example 15-3 Synthesis of Compound 15-C

Compound 15-C (32.0 g, yield 88%; MS: [M+H]⁺=363) was obtained in thesame manner as in Synthesis Example 1-4 except that 4-bromobenzaldehyde(18.5 g, 100.0 mmol) was used instead of acetaldehyde.

Synthesis Example 15-4 Synthesis of Chemical Formula 1-1-25

A compound of Chemical Formula 1-1-25 (18.5 g, yield 69%; MS:[M+H]⁺=537) was obtained in the same manner as in Synthesis Example 1-5except that Compound 15-B (18.2 g, 50.0 mmol) was used instead ofCompound 1-D.

Synthesis Example 16 Synthesis of Chemical Formula 1-6-17

Synthesis Example 16-1 Synthesis of Compound 16-A

Compound 16-A (47.0 g, yield 69%; MS: [M+H]⁺=353) was obtained in thesame manner as in Synthesis Example 1-1 except that2-amino-6-bromophenol (25.0 g, 192.5 mmol) was used instead of2-aminophenol.

Synthesis Example 16-2 Synthesis of Compound 16-B

Compound 16-B (28.5 g, yield 72%; MS: [M+H]⁺=306) was obtained in thesame manner as in Synthesis Example 1-2 except that Compound 16-A (45.6g, 128.9 mmol) was used instead of Compound 1-A.

Synthesis Example 16-3 Synthesis of Compound 16-C

Compound 16-C (28.3 g, yield 97%; MS: [M+H]⁺=276) was obtained in thesame manner as in Synthesis Example 1-3 except that Compound 16-B (32.4g, 105.4 mmol) was used instead of Compound 1-B.

Synthesis Example 16-4 Synthesis of Compound 16-D

Compound 16-D (32.3 g, yield 89%; MS: [M+H]⁺=363) was obtained in thesame manner as in Synthesis Example 1-4 except that Compound 16-C (27.7g, 100 mmol) was used instead of Compound 1-C, and benzaldehyde (10.6 g,100.0 mmol) was used instead of acetaldehyde.

Synthesis Example 16-5 Synthesis of Chemical Formula 1-6-17

Chemical Formula 1-6-17 (16.5 g, yield 54%; MS: [M+H]⁺=613) was obtainedin the same manner as in Synthesis Example 1-5 except that Compound 16-D(18.2 g, 50.0 mmol) was used instead of Compound 1-D, and(4-(10-phenylanthracen-9-yl)phenyl)boronic acid (18.7 g, 50.0 mmol) wasused instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 17 Synthesis of Chemical Formula 1-7-17

Synthesis Example 17-1 Synthesis of Compound 17-A

Compound 17-A (57.3 g, yield 84%; MS: [M+H]⁺=353) was obtained in thesame manner as in Synthesis Example 1-1 except that2-amino-4-bromophenol (25.0 g, 192.5 mmol) was used instead of2-aminophenol.

Synthesis Example 17-2 Synthesis of Compound 17-B

Compound 17-B (27.3 g, yield 69%; MS: [M+H]⁺=306) was obtained in thesame manner as in Synthesis Example 1-2 except that Compound 17-A (45.6g, 128.9 mmol) was used instead of Compound 1-A.

Synthesis Example 17-3 Synthesis of Compound 17-C

Compound 17-C (28.9 g, yield 99%; MS: [M+H]⁺=276) was obtained in thesame manner as in Synthesis Example 1-3 except that Compound 17-B (32.4g, 105.4 mmol) was used instead of Compound 1-B.

Synthesis Example 17-4 Synthesis of Compound 17-D

Compound 17-D (26.2 g, yield 83%; MS: [M+H]⁺=315) was obtained in thesame manner as in Synthesis Example 1-4 except that Compound 17-C (27.7g, 100 mmol) was used instead of Compound 1-C, and propionaldehyde (7.2ml, 100.0 mmol) was used instead of acetaldehyde.

Synthesis Example 17-5 Synthesis of Chemical Formula 1-7-17

A compound of Chemical Formula 1-7-17 (18.9 g, yield 67%; MS:[M+H]⁺=565) was obtained in the same manner as in Synthesis Example 1-5except that Compound 17-D (18.2 g, 50.0 mmol) was used instead ofCompound 1-D, and 4-(10-phenylanthracen-9-yl)phenyl)boronic acid (18.7g, 50.0 mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 18 Synthesis of Chemical Formula 1-8-17

Synthesis Example 18-1 Synthesis of Compound 18-A

Compound 18-A (53.2 g, yield 78%; MS: [M+H]⁺=353) was obtained in thesame manner as in Synthesis Example 1-1 except that2-amino-3-bromophenol (25.0 g, 192.5 mmol) was used instead of2-aminophenol.

Synthesis Example 18-2 Synthesis of Compound 18-B

Compound 18-B (28.9 g, yield 73%; MS: [M+H]⁺=306) was obtained in thesame manner as in Synthesis Example 1-2 except that Compound 18-A (45.6g, 128.9 mmol) was used instead of Compound 1-A.

Synthesis Example 18-3 Synthesis of Compound 18-C

Compound 18-C (28.6 g, yield 98%; MS: [M+H]⁺=276) was obtained in thesame manner as in Synthesis Example 1-3 except that Compound 18-B (32.4g, 105.4 mmol) was used instead of Compound 1-B.

Synthesis Example 18-4 Synthesis of Compound 18-D

Compound 18-D (27.8 g, yield 88%; MS: [M+H]⁺=315) was obtained in thesame manner as in Synthesis Example 1-4 except that Compound 18-C (27.7g, 100 mmol) was used instead of Compound 1-C, and propionaldehyde (7.2ml, 100.0 mmol) was used instead of acetaldehyde.

Synthesis Example 18-5 Synthesis of Chemical Formula 1-8-17

A compound of Chemical Formula 1-8-17 (14.4 g, yield 51%; MS:[M+H]⁺=565) was obtained in the same manner as in Synthesis Example 1-5except that Compound 18-D (18.2 g, 50.0 mmol) was used instead ofCompound 1-D, and 4-(10-phenylanthracen-9-yl)phenyl)boronic acid (18.7g, 50.0 mmol) was used instead of (10-phenylanthracen-9-yl)boronic acid.

Synthesis Example 19 Synthesis of Chemical Formula 1-5-1

Synthesis Example 19-1 Synthesis of Compound 19-A

Compound 1-D (21.1 g, 70.0 mmol), bis(pinacolato)diborone (19.6 g, 77.0mmol), potassium acetate (20.6 g, 210 mmol),[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.2 g, 2.1mmol) and tricyclohexylphosphine (1.2 g, 2.4 mmol) were placed indioxane (350 ml), and the mixture was refluxed for 12 hours. After thereaction was complete, the result was cooled to room temperature, andvacuum distilled to remove the solvent. The result was dissolved inchloroform, washed three times with water, and the organic layer wasseparated and dried using magnesium sulfate. The resulting organic layerwas vacuum distilled to obtain Compound 19-A (21.0 g, yield 86%; MS:[M+H]⁺=349).

Synthesis Example 19-2 Synthesis of Chemical Formula 1-5-1

Compound 19-A (17.4 g, 50 mmol) and (4-bromophenyl)diphenylphosphineoxide (17.9 g, 50 mmol) were dissolved in tetrahydrofuran (THF). A 2Mpotassium carbonate (K₂CO₃) solution (72 mL) and thentetrakis(triphenylphosphine) palladium(0) (1.10 g, 1.91 mmol) were addedthereto, and the result was refluxed for 3 hours. After the reaction wascomplete, the result was cooled to room temperature, filtered, and thenwashed with water and ethanol. The filtered solid product was purifiedby column chromatography using tetrahydrofuran/hexane (THF/Hexane:1/4)to obtain a compound of Chemical Formula 1-5-1 (15.5 g, yield 62%; MS:[M+H]⁺=499).

Synthesis Example 20 Synthesis of Chemical Formula 1-5-2

Synthesis Example 20-1 Synthesis of Chemical Formula 1-5-2

A compound of Chemical Formula 1-5-2 (14.5 g, yield 53%; MS: [M+H]⁺=549)was obtained in the same manner as in Synthesis Example 19-2 except that(6-bromonaphthalen-2-yl)diphenylphosphine oxide (20.4 g, 50 mmol) wasused instead of (4-bromophenyl)diphenylphosphine oxide.

Synthesis Example 2-1 Synthesis of Chemical Formula 2-2-1

A compound of Chemical Formula 2-2-1 (21.8 g, yield 30%; MS: [M+H]⁺=491)was obtained in the same manner as in Synthesis Example 1 except that2-amino-5-bromobenzenethiol (39.3 g, 192.5 mmol) was used instead of2-amino-5-bromophenol.

Synthesis Example 2-2 Synthesis of Chemical Formula 2-3-17

A compound of Chemical Formula 2-3-17 (22.3 g, yield 26%; MS:[M+H]⁺=581) was obtained in the same manner as in Synthesis Example 17except that 2-amino-4-bromobenzenethiol (39.3 g, 192.5 mmol) was usedinstead of 2-amino-4-bromophenol.

Synthesis Example 2-3 Synthesis of Chemical Formula 2-3-1

A compound of Chemical Formula 2-3-1 (17.2 g, yield 23%; MS: [M+H]⁺=505)was obtained in the same manner as in Synthesis Example 17 except that2-amino-4-bromobenzenethiol (39.3 g, 192.5 mmol) was used instead of2-amino-4-bromophenol, (10-phenylanthracen-9-yl)boronic acid (14.9 g,50.0 mmol) was used instead of(4-(10-phenylanthracen-9-yl)phenyl)boronic acid.

Synthesis Example 2-4 Synthesis of Chemical Formula 2-4-1

Synthesis Example 2-4-1 Synthesis of Compound 2-4-A

Compound 2-1-D (22.2 g, 70.0 mmol), bis(pinacolato)diborone (19.6 g,77.0 mmol), potassium acetate (20.6 g, 210 mmol),[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.2 g, 2.1mmol) and tricyclohexylphosphine (1.2 g, 2.4 mmol) were placed intetrahydrofuran (350 ml), and the mixture was refluxed for 12 hours.After the reaction was complete, the result was cooled to roomtemperature, and vacuum distilled to remove the solvent. The result wasdissolved in chloroform, washed three times with water, and the organiclayer was separated and dried using magnesium sulfate. The resultingorganic layer was vacuum distilled to obtain Compound 2-4-A (19.4 g,yield 76%; MS: [M+H]⁺=365).

Synthesis Example 2-4-2 Synthesis of Chemical Formula 2-4-1

A compound of Chemical Formula 2-4-1 (18.3 g, yield 71%; MS: [M+H]⁺=515)was obtained in the same manner as in Synthesis Example 19-2 except thatCompound 2-4-A (18.2 g, 50 mmol) was used instead of Compound 19-A.

EXPERIMENTAL EXAMPLE Experimental Example 1-1

A glass substrate on which indium tin oxide (ITO) was coated as a thinfilm to a thickness of 500 Å was placed in distilled water, in which adetergent is dissolved, and ultrasonic cleaned. As the detergent, aproduct of Fischer Corporation was used, and as the distilled water,distilled water filtered twice with a filter manufactured by MilliporeCorporation was used. After the ITO was cleaned for 30 minutes,ultrasonic cleaning was repeated twice for 10 minutes using distilledwater. After the cleaning with distilled water was finished, thesubstrate was ultrasonic cleaned with isopropyl alcohol, acetone andmethanol solvents, and dried, and then transferred to a plasma cleaner.In addition, the substrate was cleaned for 5 minutes using oxygenplasma, and then transferred to a vacuum depositor.

On the transparent ITO electrode prepared as above, a hole injectionlayer was formed to a thickness of 100 Å by thermal vacuum depositinghexanitrile hexaazatriphenylene (HAT) of the following Chemical Formula.

A hole transfer layer was formed on the hole injection layer by vacuumdepositing 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (1,000Å) of the Chemical Formula shown above.

Subsequently, a light emitting layer was formed on the hole transferlayer to a film thickness of 230 Å by vacuum depositing GH and GD shownbelow in a weight ratio of 10:1.

An electron injection and transfer layer was formed on the lightemitting layer to a thickness of 350 Å by vacuum depositing the compoundof Chemical Formula 1-2-1.

A cathode was formed on the electron injection and transfer layer bydepositing lithium fluoride (LiF) to a thickness of 15 Å and aluminum toa thickness of 2,000 Å in consecutive order.

In the above process, the deposition rates of the organic materials weremaintained at 0.4 to 0.7 Å/sec, the deposition rates of the lithiumfluoride and the aluminum of the cathode were maintained at 0.3 Å/secand 2 Å/sec, respectively, and the degree of vacuum when being depositedwas maintained at 2×10⁻⁷ to 5×10⁻⁶ torr, and as a result, an organiclight emitting device was manufactured.

Comparative Example 1

An organic light emitting device was manufactured in the same manner asin Experimental Example 1-1 except that a compound of the followingChemical Formula ET-A was used instead of the compound of ChemicalFormula 1-2-1.

Experimental Examples 1-2 to 1-16

Organic light emitting devices of Experimental Examples 1-2 to 1-16 weremanufactured in the same manner as in Experimental Example 1-1 exceptthat each compound shown in Table 1 was used instead of the compound ofChemical Formula 1-2-1.

Current (10 mA/cm²) was applied to the organic light emitting devicesmanufactured in Experimental Examples 1-1 to 1-16 and ComparativeExample 1, and the results are shown in Table 1.

TABLE 1 Voltage Efficiency Color Coordinate Compound (V) (dc/A) (x, y)Experimental 1-2-1 3.89 42.15 (0.373, 0.620) Example 1-1 Experimental1-3-1 3.87 42.34 (0.373, 0.620) Example 1-2 Experimental 1-3-4 3.8342.12 (0.372, 0.621) Example 1-3 Experimental 1-3-5 3.84 41.99 (0.371,0.622) Example 1-4 Experimental 1-3-6 3.80 41.98 (0.371, 0.620) Example1-5 Experimental 1-3-12 3.86 42.10 (0.371, 0.619) Example 1-6Experimental 1-3-18 3.83 41.87 (0.372, 0.620) Example 1-7 Experimental1-3-19 3.85 41.18 (0.372, 0.621) Example 1-8 Experimental 1-4-1 3.7840.99 (0.373, 0.622) Example 1-9 Experimental 1-5-25 3.78 41.12 (0.374,0.623) Example 1-10 Experimental 1-6-17 3.81 42.22 (0.373, 0.624)Example 1-11 Experimental 1-7-17 3.82 42.12 (0.373, 0.621) Example 1-12Experimental 1-8-17 3.80 42.14 (0.372, 0.622) Example 1-13 Experimental2-2-1 3.92 41.10 (0.373, 0.620) Example 1-14 Experimental 2-3-1 3.9441.13 (0.374, 0.621) Example 1-15 Experimental 2-3-17 3.91 41.12 (0.373,0.621) Example 1-16 Comparative ET-A 3.98 39.99 (0.373, 0.621) Example 1

As seen from the results of Table 1, it was shown that the heterocycliccompound according to one embodiment of the present specification may beused as an organic material layer material of an organic light emittingdevice, and particularly when the heterocyclic compound was used in anelectron injection and transfer layer among the organic material layers,the organic light emitting device exhibited superior properties inefficiency, driving voltage, stability and the like. In particular, itwas demonstrated that the compound exhibited superior properties due toexcellent thermal stability, a deep HOMO level, and hole stability. Thecompound has an advantage in that it improves the efficiency of anorganic light emitting device, and may improve the stability of a devicedue to the thermal stability of the compound.

Experimental Example 2-1

On the transparent ITO electrode prepared as in Experimental Example1-1, a hole injection layer was formed to a thickness of 100 Å bythermal vacuum depositing hexanitrile hexaazatriphenylene (HAT) of theChemical Formula shown above.

A hole transfer layer was formed on the hole injection layer by vacuumdepositing 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (700 Å),hexanitrile hexaazatriphenylene (HAT) (50 Å) and4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (700 Å) of thechemical formulae shown above in consecutive order.

Subsequently, a light emitting layer was formed on the hole transferlayer to a film thickness of 200 Å by vacuum depositing BH and BD shownbelow in a weight ratio of 25:1.

An electron injection and transfer layer was formed on the lightemitting layer to a thickness of 300 Å by vacuum depositing the compoundof Chemical Formula 1-2-1 and lithium quinalate (LiQ) of the followingChemical Formula in a weight ratio of 1:1.

A cathode was formed on the electron injection and transfer layer bydepositing lithium fluoride (LiF) to a thickness of 15 Å and aluminum toa thickness of 2,000 Å in consecutive order.

In the above process, the deposition rates of the organic materials weremaintained at 0.4 to 0.7 Å/sec, the deposition rates of the lithiumfluoride and the aluminum of the cathode were maintained at 0.3 Å/secand 2 Å/sec, respectively, and the degree of vacuum when being depositedwas maintained at 2×10⁻⁷ to 5×10⁻⁶ torr, and as a result, an organiclight emitting device was manufactured.

Comparative Example 2

An organic light emitting device was manufactured in the same manner asin Experimental Example 2-1 except that a compound of the followingChemical Formula ET-A was used instead of the compound of ChemicalFormula 1-2-1.

Experimental Example 2-2 to 2-14

Organic light emitting devices of Experimental Examples 2-2 to 2-14 weremanufactured in the same manner as in Experimental Example 2-1 exceptthat each compound shown in Table 2 was used instead of the compound ofChemical Formula 1-2-1.

Current (10 mA/cm²) was applied to the organic light emitting devicesmanufactured in Experimental Examples 2-1 to 2-14 and ComparativeExample 2, and the results are shown in Table 2.

TABLE 2 Voltage Efficiency Color Coordinate Compound (V) (dc/A) (x, y)Experimental 1-2-1 3.81 5.31 (0.141, 0.130) Example 2-1 Experimental1-3-1 3.85 5.24 (0.141, 0.130) Example 2-2 Experimental 1-3-26 3.86 5.30(0.142, 0.131) Example 2-3 Experimental 1-3-28 3.87 5.29 (0.140, 0.129)Example 2-4 Experimental 1-3-29 3.79 5.28 (0.139, 0.129) Example 2-5Experimental 1-3-30 3.86 4.29 (0.141, 0.131) Example 2-6 Experimental1-3-34 3.79 5.27 (0.140, 0.131) Example 2-7 Experimental 1-4-1 3.81 5.32(0.140, 0.130) Example 2-8 Experimental 1-1-25 3.83 5.28 (0.142, 0.129)Example 2-9 Experimental 1-5-1 3.80 5.30 (0.142, 0.130) Example 2-10Experimental 1-5-2 3.82 5.28 (0.141, 0.131) Example 2-11 Experimental2-2-1 3.90 5.18 (0.141, 0.130) Example 2-12 Experimental 2-3-1 3.89 5.12(0.140, 0.130) Example 2-13 Experimental 2-4-1 3.98 5.15 (0.141, 0.131)Example 2-14 Comparative ET-A 4.05 4.75 (0.141, 0.129) Example 2

As seen from the results of Table 2, it was shown that the heterocycliccompound according to one embodiment of the present specification may beused as an organic material layer material of an organic light emittingdevice, and particularly when the heterocyclic compound was used in anelectron injection and transfer layer among the organic material layers,the organic light emitting device exhibited superior properties inefficiency, driving voltage, stability and the like. In particular, itwas demonstrated that the compound exhibited superior properties due toexcellent thermal stability, a deep HOMO level, and hole stability. Thecompound may be used either alone or as a mixture with an n-type dopantsuch as LiQ in an organic electronic device including an organic lightemitting device. The compound has an advantage in that it improves theefficiency of an organic light emitting device, and may improve thestability of a device due to the thermal stability of the compound.

1. An organic light emitting device comprising: a first electrode; asecond electrode provided opposite to the first electrode; and one ormore organic material layers including a light emitting layer providedbetween the first electrode and the second electrode, wherein one ormore layers of the organic material layers include the heterocycliccompound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1, X is O or S; R1 is deuterium; a halogengroup; a nitrile group; a nitro group; a hydroxyl group; a carbonylgroup; an ester group; an imide group; an amide group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted silyl group; a substituted or unsubstitutedboron group; a substituted or unsubstituted alkylamine group; asubstituted or unsubstituted aralkylamine group; a substituted orunsubstituted arylamine group; a substituted or unsubstitutedheteroarylamine group; a substituted or unsubstituted arylphosphinegroup; a substituted or unsubstituted phosphine oxide group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroring group including one or more of N, O and Satoms; and R2 to R8 are the same as or different from each other, andeach independently hydrogen; deuterium; a halogen group; a nitrilegroup; a nitro group; a hydroxyl group; a carbonyl group; an estergroup; an imide group; an amide group; a substituted or unsubstitutedalkyl group; a substituted or unsubstituted cycloalkyl group; asubstituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted silyl group; a substituted or unsubstitutedboron group; a substituted or unsubstituted alkylamine group; asubstituted or unsubstituted aralkylamine group; a substituted orunsubstituted arylamine group; a substituted or unsubstitutedheteroarylamine group; a substituted or unsubstituted arylphosphinegroup; a substituted or unsubstituted phosphine oxide group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroring group including one or more of N, O and Satoms, or adjacent groups among R2 to R8 bond to each other to form analiphatic ring, an aromatic ring, an aliphatic heteroring or an aromaticheteroring, or form a spiro bond.
 2. The organic light emitting deviceof claim 1, wherein R1 is a substituted or unsubstituted alkyl group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted aryl group; a substituted or unsubstituted phosphine oxidegroup; or a substituted or unsubstituted heteroring group including oneor more of N, O and S atoms.
 3. The organic light emitting device ofclaim 1, wherein at least one of R1 to R8 is any one of the followingstructures:


4. The organic light emitting device of claim 1, wherein theheterocyclic compound represented by Chemical Formula 1 is representedby any one of the following Chemical Formulae 1-1-1 to 1-1-64 and 2-1-1to 2-1-10:


5. The organic light emitting device of claim 1, wherein the organicmaterial layer includes an electron transfer layer, an electroninjection layer or a layer carrying out electron transfer and electroninjection at the same time, and the electron transfer layer, theelectron injection layer or the layer carrying out electron transfer andelectron injection at the same time includes the heterocyclic compound.6. The organic light emitting device of claim 5, wherein the electrontransfer layer, the electron injection layer or the layer carrying outelectron transfer and electron injection at the same time is formed onlywith the heterocyclic compound.
 7. The organic light emitting device ofclaim 5, wherein the electron transfer layer, the electron injectionlayer or the layer carrying out electron transfer and electron injectionat the same time includes the heterocyclic compound as a p-type host,and an n-type dopant as a dopant.
 8. The organic light emitting deviceof claim 7, wherein the n-type dopant includes alkali metals, alkalimetal compounds, alkaline earth metals, alkaline earth metal compounds,or combinations thereof.
 9. The organic light emitting device of claim1, wherein the light emitting layer includes the heterocyclic compoundas a host, and a phosphorous dopant compound as a dopant.
 10. Theorganic light emitting device of claim 1, wherein the organic materiallayer further includes one, two or more layers selected from the groupconsisting of a hole injection layer, a hole transfer layer, an electrontransfer layer, an electron injection layer, an electron blocking layerand a hole blocking layer.
 11. A heterocyclic compound represented bythe following Chemical Formula 3:

wherein, in Chemical Formula 3, X is O or S; R1 is deuterium; a halogengroup; a nitrile group; a nitro group; a hydroxyl group; a carbonylgroup; an ester group; an imide group; an amide group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted silyl group; a substituted or unsubstitutedboron group; a substituted or unsubstituted alkylamine group; asubstituted or unsubstituted aralkylamine group; a substituted orunsubstituted arylamine group; a substituted or unsubstitutedheteroarylamine group; a substituted or unsubstituted arylphosphinegroup; a substituted or unsubstituted phosphine oxide group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroring group including one or more of N, O and Satoms; R2 to R8 are the same as or different from each other, and eachindependently hydrogen; deuterium; a halogen group; a nitrile group; anitro group; a hydroxyl group; a carbonyl group; an ester group; animide group; a substituted or unsubstituted alkyl group; a substitutedor unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted alkylamine group; a substituted or unsubstitutedaralkylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted heteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroring group including one or more ofN, O and S atoms, or adjacent groups among R2 to R8 bond to each otherto form an aliphatic ring, an aromatic ring, an aliphatic heteroring oran aromatic heteroring, or form a spiro bond; and at least one of R2 toR8 is a substituted or unsubstituted alkyl group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted aryl group;a substituted or unsubstituted phosphine oxide group; or a substitutedor unsubstituted heteroring group including one or more of N, O and Satoms.
 12. The heterocyclic compound of claim 11, wherein R1 is asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedalkenyl group; a substituted or unsubstituted aryl group; a substitutedor unsubstituted phosphine oxide group; or a substituted orunsubstituted heteroring group including one or more of N, O and Satoms.
 13. The heterocyclic compound of claim 11, wherein R2 to R8 arethe same as or different from each other, and each dependently hydrogen;an alkyl group; an alkenyl group; an aryl group; a phosphine oxidegroup; or a heteroring group including one or more of N, O and S atoms;and the alkyl group; the alkenyl group; the aryl group; the phosphineoxide group; and the heteroring group including one or more of N, O andS atoms are unsubstituted or substituted with one, two or moresubstituents selected from the group consisting of deuterium, a nitrilegroup, a substituted or unsubstituted alkyl group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted silane group, a substituted orunsubstituted phosphine oxide group, and a substituted or unsubstitutedheteroring group including one or more of N, O and S atoms, or two ormore substituents bond to each other to form an aliphatic ring, anaromatic ring, an aliphatic heteroring or an aromatic heteroring, orform a spiro bond.
 14. The heterocyclic compound of claim 11, wherein atleast one of R2 to R8 is any one of the following structures:


15. The heterocyclic compound of claim 11, wherein the heterocycliccompound represented by Chemical Formula 3 is represented by any one ofthe following structures:


16. The heterocyclic compound of claim 11, wherein the heterocycliccompound represented by Chemical Formula 3 is represented by any one ofthe following structures: